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Lithiated Azafulvenes by Halogen/Metal Interchange of Brominated 6‐(Diisopropylamino)‐1‐azafulvene Derivatives. Novel synthesis of 5‐mono‐ and 4,5‐disubstituted 1 H ‐pyrrole‐2‐carbaldehydes
Author(s) -
Bray Brian L.,
Hess Petr,
Muchowski Joseph M.,
Scheller Markus E.
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710823
Subject(s) - chemistry , halogen , pyrrole , reagent , hydrolysis , metal , organic chemistry , bromine , combinatorial chemistry , medicinal chemistry , alkyl
The first known lithiated 1‐azafulvene derivatives were generated by low‐temperature halogen/metal interchange, with t ‐BuLi, from the corresponding brominated 6‐diisopropylamino compounds 3b and 12 . These Li species reacted with sundry eletrophilic reagents to give products which, on basic hydrolysis, were converted into 5‐mono‐ or 4,5‐disubstituted pyrrole‐2‐carbaldehydes 10 and 16 , respectively.